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Harvard Business Review (Nov, 2010)
Changing Gender On the Job
A Microsoft executive describes her difficult decision to “transition” at work—and the
unexpected benefits.
by Daniel McGinn
As an up-and-coming manager at Microsoft, Michael Wallent had a reputation for being a
tough boss—at times, a bit too tough. He had joined the company in 1996 and advanced
quickly; by 1999 he was overseeing a team of 300 engineers who worked on developing
Internet Explorer. Like Microsoft’s founder, Bill Gates, who met with Wallent to review his
team’s work each quarter, Wallent focused on data and facts, not employees’ feelings, and
was known for delivering withering criticism in product-review sessions. His typical
comments: “This is stupid.” “This is wrong.” “This is what you need to do.” Debra Chrapaty,
his former boss (who’s now at Cisco), says, “Michael was known to be aggressive, a little bit
condescending, harsh—he had an arrogant engineering mind-set.”
That’s in stark contrast to the style of Megan Wallent. She’s also one of Microsoft’s best and
brightest, who as a general manager ranks among the top 1% of the company’s 89,000
employees and oversees 350 engineers developing user interfaces for server software. Her
employees praise her as a boss with high emotional intelligence. She speaks softly and asks
probing questions to help them find solutions on their own. “Megan is relaxed,” says Angel
Calvo, a director of test engineering who’s been at Microsoft for 19 years. “She really thinks
about how people are going to feel about particular decisions.”
Two bosses, two styles—but only one person. In 2007 Michael Wallent told colleagues he
was transgendered, took a six-week leave to undergo breast implantation and facial
feminization surgeries, and returned to Microsoft in early 2008 as Megan. “Going through the
transition was tremendously complicated,” she says, but she tried to approach it like a
standard business problem. “I told my managers this was going to happen and that I was
going to partner with them on how to make it successful for the company.” Although her
bosses were supportive, says Anh Hoang, Wallent’s wife (and a former Microsoft employee),
the process was fraught with anxiety. “We knew this could be a careerlimiting move for her,”
Hoang says. “She’s probably one of the most senior people at any company to go through
this, so she was essentially breaking new ground.”
Looking back, Wallent says that her transition from man to woman transformed her approach
to management, which may ultimately help her career. “I’ve gotten better at my job,” she
says, “just through being more open, honest, and transparent, and learning how to better
communicate with people.”
Like many people with gender identity disorder, Michael Wallent always had a vague sense
that his anatomy didn’t match up with his sense of self. But that inner conflict stayed in the
background as he studied engineering at Worcester Polytechnic Institute, married, and moved
to Seattle to join Microsoft. By 2005 he’d had two children, divorced his first wife, and
remarried. He’d shifted from running the Internet Explorer group to overseeing a team that
helped design the look and feel of the Windows Vista operating system. In 2007, at age 38
and just two months after he and Hoang had had a child, he told her he was transgendered. A
few months later—and with her support—he decided he would transition to living as a
woman, and scheduled surgery for late that year.
A few months before the surgery, Wallent asked his boss for a meeting. Chrapaty had been
complaining about Microsoft’s struggle to recruit and hire women, so Wallent broke the ice
by saying, “Debra, I’ve decided to do something to increase the diversity of the team, and I’m
starting with me.” Although Chrapaty had helped lead Microsoft’s coalition of gay, lesbian,
bisexual, and transgendered employees, she was shocked. “I was trying to place it in the
context of this superpositioned male executive who’d just come off paternity leave with his
wife and baby,” she says. But after a moment of confusion, she offered her help.
At most companies the HR department takes charge of announcing a transition to
employees. Wallent rejected this approach.
Over the next few weeks, Wallent held one-on-one meetings with his dozen direct reports to
let them know about his coming change. (As he did when telling his family, he started with
those he expected would be most supportive and worked his way up to the harder cases.) He
sent e-mails to several key Microsoft executives, including Gates and CEO Steve Ballmer,
both of whom replied offering encouragement. Then he sent a message to all 100 members of
his team, its unusual contents flagged with a simple subject line—“Re: Me.”
Gender transitions at work remain relatively rare. Jillian Weiss, a consultant and an associate
professor at Ramapo College who’s studied the issue, says there are no reliable statistics, but
her work suggests that companies with more than 2,000 employees located in places with
tolerant populations are likely to face it at some point. Still, some transgendered employees
encounter so much resistance from coworkers that they end up leaving their jobs. (That’s a
particularly unfortunate outcome, since transgendered people typically have a harder time
finding new work, Weiss says, in part because of their appearance.) At most companies the
HR department takes charge of announcing the news to employees, usually by holding a
meeting without the transitioning worker in attendance in order to encourage a frank
discussion of concerns. Weiss compares the process to announcing a layoff. “If you’re going
to do something that creates anxiety for people, you have to give them information to ease
their sense of anxiety,” she says.
Wallent rejected this standard approach. “It was critical for me to own the communications
process,” she says, citing two reasons: First, relying on others might suggest she was
ashamed of the decision, which she wasn’t. Second, she believed that brutal honesty—and a
willingness to answer questions, no matter how personal—would shorten the time it took for
the news to stop being watercooler gossip.
The process wasn’t entirely smooth. Gender identity disorder is classified by the DSM as a
mental illness and is considered immoral by various religions. Even at a progressive
employer like Microsoft, it was inevitable that some workers would be uncomfortable with
Wallent’s transition. One employee mentioned that discomfort when he resigned, though it’s
unclear how big a role it actually played in his decision to leave. Wallent, who’d promised to
hear all employee questions, had to face some tough ones. In team meetings prior to his
surgery, he was asked whether he planned to stay married (yes), whether he was attracted to
men or women (women), how he intended to deal with his hairy arms (laser treatments), and
which bathroom he would use upon his return to work (the ladies’ room).
Although the sessions were difficult, Wallent now views them as a crucial part of her
transition. “A lot of people came back to me with these incredibly personal stories about
things that had happened to them that were equally transformative,” she recalls. Ultimately,
she thinks her new management style has little to do with the estrogen pills she takes daily.
She believes that it’s a by-product of those intimate conversations with her colleagues. “They
really brought home the value of authentic leadership, and of letting the people on your team
in to see your whole self,” she says. “It makes them more comfortable in their jobs.”
For employees who never knew Megan as Michael (now the majority of her team, owing to
job changes and the passage of time), her transition feels like a nonevent; what they know
about it comes only through secondhand observations and recollections. “I’ve heard she
speaks with a quieter voice now,” says Angie Anderson, a project unit manager who’s
worked for Wallent for two years. “People think she’s a better manager.”
But employees who worked for both Michael and Megan say they continue to notice the
change. Calvo, the director of test engineering, recalls that when Michael offered feedback on
prototype software, “people would leave the room paralyzed—‘Wow, I almost got fired’—
because of his directness, his bluntness.” But, he says, “Megan has a completely different
approach. She still comes to the same conclusion, but she drives people in a more emotional
way. ‘Have you thought about this?’ She’s becoming more of a coach, instead of a general.”
Wallent, who’d promised to hear all employee questions, faced some tough ones prior to
his surgery—such as, did he plan to stay married?
On most days, Wallent looks upon her gender transition as a closed chapter in her
professional life. Still, she continues to worry about whether she’ll “pass” as a woman while
representing Microsoft on customer visits and whether clients who recognize her as
transgendered will react badly. (So far they haven’t, she says.) There are also periodic
reminders of her unique status: For instance, she’s still officially listed as a man for HR
purposes, partly to avoid tax and legal problems.
Her worries about imperiling her career, however, seem to have been unfounded. She is
currently one level below vice president, and on the basis of her performance reviews, she
thinks she’s on track to eventually be promoted—perhaps faster than Michael would have
been, because of her evolving leadership style. Whereas Michael relied on technical expertise
as the key to his authority, Megan says her focus is people. “I want to be the type of leader
that helps people achieve their full potential, and to get the most out of them every day,” she
says. “That’s been part of my transition—learning how to lead from the people.”
Daniel McGinn is a senior editor at Harvard Business Review.